Michael, a 40-something divorced man, has spent three years moping after his divorce. His best friend and former drill sergeant, Paul, convinces him to start dating again. Michael meets Jennifer, the woman of his dreams, at a trade show only to discover that she is Paul's long-estranged daughter, all grown up. They try to keep their relationship a secret from Paul, but when he stumbles upon them kissing in a local restaurant, all hell breaks loose. As the men's life-long friendship hangs in the balance, Jennifer, prodded by Michael's nerdy employee, Derek, takes a big risk with an attempted reconciliation with her father. PS, I Love Your Daughter examines what happens when the all-too-rare close friendships between men stumble over family and romance.